Pick Your Perk with Windstar Cruises

It's that time of year - Windstar's Pick Your Perk offer is back for another season of savings!

Book by Jun 30, 2025

Leave the crowds and clichés behind on small, elegant ships that carry less than 350 pampered, privileged guests. Enjoy late-night departures, overnights in port, and one-of-a-kind tours and activities. Connect to the wonder, authenticity, and majesty of a world discovered in private-yacht style. With access to small ports, you’ll visit popular must-sees as well as the best-kept secrets.

PICK YOUR PERK
Book today and enjoy Pick Your Perk to enhance your Windstar cruise the way you want. Choose from;

- Up to US $1,000 Onboard Credit per suite OR
- One Free Pre or Post Hotel Night OR
- Free Upgrade to All-Inclusive Fares for Premium Suites Guests

Plus, on 2025 sailings enjoy a reduced deposit!

Our Exclusive Bonus: On select sailings you'll receive up to $300 Onboard Credit per stateroom.

LOOKING FOR MORE INCLUSIONS? Add Windstar's All-Inclusive cruise pricing for only US $89 extra per guest, per day includes unlimited alcoholic beverages, unlimited Wi-Fi, and all gratuities.

Featured Windstar sailings

Ask for cruises fares on these and other available departures.

Around IcelandAug 04, 2025 (7 days)

Star Pride | Roundtrip Reykjavik

PICK YOUR PERK
Choose One of the following: $100 Onboard Credit per guest OR One Free Pre or Post Hotel Night OR if you upgrade to a Premium Suite you'll receive a Free Upgrade to the All-Inclusive Fare.

Exclusive Bonus: Up to $300 Onboard Credit per stateroom.

Dramatic scenery and curious communities coalesce on this week-long circumnavigation of Iceland. Explore a country few people will ever visit, and go far beyond the tourist hotspots to remote fjords, raging waterfalls, and small fishing villages. Get to know the independent and creative Icelanders, and watch whales and seabirds play offshore. This Iceland cruise is yachting at its most inventive.

Southeast Canadian ExplorationsSep 26, 2025 (11 days)

Star Pride | Boston to Montreal

PICK YOUR PERK
Choose One of the following: $100 Onboard Credit per guest OR One Free Pre or Post Hotel Night OR if you upgrade to a Premium Suite you'll receive a Free Upgrade to the All-Inclusive Fare.

Exclusive Bonus: Up to $300 Onboard Credit per stateroom.

Quebec’s French-flavored history, the fusion of Acadian and Scottish cultures in Nova Scotia—each province distills its own blend of Old World and New, bucolic and urbane. Overnight in Quebec City and browse the shops and boulangeries along picturesque Petit Champlain, the oldest street in North America. Fall under the spell of UNESCO site Lunenburg’s charming waterfront, and Halifax with its lively pub culture and majestic Citadel. Take in the brilliance of New England’s fall colors and the historic sites of Boston, one of America’s oldest cities.

The Colorful Canary IslandsNov 12, 2025 (8 days)

Wind Star | Lisbon to Santa Cruz de Tenerife

PICK YOUR PERK
Choose One of the following: $100 Onboard Credit per guest OR One Free Pre or Post Hotel Night OR if you upgrade to a Premium Suite you'll receive a Free Upgrade to the All-Inclusive Fare. PLUS, a Reduced Deposit on this departure!

Exclusive Bonus: Up to $300 Onboard Credit per stateroom.

Volcanoes have left their mark everywhere here – on snow-capped Mount Teide, on black sand beaches, in rich soils and natural sea pools – yet each island is unique. Palms, pines, vineyards, and banana plantations each offer their own shade of green. On some islands you’ll see terraced farms clinging to valley walls. On others, trails trace the cliffs and reward hikers with breathtaking ocean views. And there’s always something new to do. Explore historic colonial towns, national parks, and nature reserves. Discover cuisines that reflect both mainland traditions and the islands’ distinctive culture and abundance. Shop for colorful pottery and jewelry made from lava. Listen to Canarian minstrels coax beautiful folk tunes from the tiny guitar known as a timple. Surround yourself with sunshine, sand, and the soul of a place that works its way into your heart and never lets go.

Beach Fun & Sun: A Remote Caribbean GetawayDec 14, 2025 (6 days)

Wind Surf | Roundtrip Philipsburg

PICK YOUR PERK
Choose One of the following: $100 Onboard Credit per guest OR One Free Pre or Post Hotel Night OR if you upgrade to a Premium Suite you'll receive a Free Upgrade to the All-Inclusive Fare. PLUS, a Reduced Deposit on this departure!

Exclusive Bonus: Up to $300 Onboard Credit per stateroom.

Bask on remote beaches resplendent in natural beauty during this relaxing, unrushed, and uncrowded 7-day getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from Windstar’s onboard Watersports Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar takes you to the secret beaches and invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.

Pick Your Perk Now!

Discover the unspoiled and unfamiliar in a style that will completely transform the way you cruise. Windstar knows the way to experience a different kind of cruise — intimate, authentic and unscripted. 180 degrees from ordinary.

Learn more about Windstar

Terms & Conditions

All fares and offers are valid at the time of publication. Fares and offers are subject to change based on availability and other considerations. Sailings of less than 14 days receive a choice of one of these added perks: All categories can choose between One complimentary hotel night** (pre or post) or onboard credit of $200 (or $100 USD per guest) for Standard Staterooms/Suites (B, BX, A, AX, TX, S, S1, SS1, S2, S3, BS, SBS, BS1, SBS1), or $400 ($200 USD per guest) for Premium Suites (Owner’s Suite, Classic Suite, Deluxe Suite, and on Wind Surf: Bridge Suite, Officer’s Suite and STE). Premium Suites have a third choice to upgrade to the All-In Package. Sailings of 14 or more days receive a choice of one of these added perks: All categories can choose between One complimentary hotel night** (pre or post) or onboard credit of $400 ($200 USD per guest) for Standard Staterooms/Suites (B, BX, A, AX, TX, S, S1, SS1, S2, S3, BS, SBS, BS1, SBS1, OV, IN, IN1, IN2, IN3, VS, VSS, VS1, VS2, VS3, VVB), or $1000 ($500 USD per guest) for Premium Suites (Owner’s Suite, Horizon Owner’s Suite, Classic Suite, Star Suite, Deluxe Suite, and on Wind Surf: Bridge Suite, Officer’s Suite and STE). Premium Suites have a third choice to upgrade to the All-In Package. Single and Triple fares will receive shipboard credit at the per guest rate. Perk selection must be locked in at least 90 days prior to sailing, Hotel option subject to availability *Exclusions: Grand Prix sailings, Seeker Inaugural sailing (1/15/26) **Pre/Post Hotel is based on availability and some restrictions apply. Not all hotels available on this offer in Rome from 4/1/25 thru 11/15/25 or Barbados on any date. Bookings are non-transferable; no name changes can be made nor can this offer be applied retroactively. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer expires on June 30, 2025. Ships’ registry: Bahamas. Reduced Deposit is Non-refundable, but can go towards another cruise if changed prior to 120 days before sailing. Consult your Windstar representative for promotional offer or discount combinability. Bookings are non-transferable; no name changes can be made nor can this offer be applied retroactively. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer expires on June 30, 2025. Ships’ registry: Bahamas.

Ellen Eisen